Acetic Anhydride → 4-[5-(Acetyloxy)-7-bromo-1,3-benzoxazol-2-yl]-2-fluorophenyl acetate

HRID 858240Notes

Reaction equation

HRID 858240 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[Br:8][C:9]1[C:17]2[O:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([F:25])[CH:19]=3)=[N:14][C:13]=2[CH:12]=[C:11]([OH:26])[CH:10]=1.[O:27]1CCO[CH2:29][CH2:28]1>CN(C)C1C=CN=CC=1.O>[C:1]([O:24][C:21]1[CH:22]=[CH:23][C:18]([C:15]2[O:16][C:17]3[C:9]([Br:8])=[CH:10][C:11]([O:26][C:28](=[O:27])[CH3:29])=[CH:12][C:13]=3[N:14]=2)=[CH:19][C:20]=1[F:25])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 312751,4-DioxaneHCID 1354573257-Bromo-2-(3-fluoro-4-hydroxyphenyl)benzo[d]oxazol-5-ol

Product 1

HCID 219073714-[5-(Acetyloxy)-7-bromo-1,3-benzoxazol-2-yl]-2-fluorophenyl acetateYield 56%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

Acetic anhydride (1.0 mL, 9.95 mmol) was added into a cold (0 ° C.) solution of 7-bromo-2-(3-fluoro-4-hydroxyphenyl)-1,3-benzoxazol-5-ol (1.24 g, 3.8 mmol), N,N-dimethylpyridin-4-amine (1.1 g, 9.18 mmol) and 1,4-dioxane (13 mL). The reaction mixture was allowed to warm up to room temperature and stirred for 20 h. Water (50 mL) was added to the reaction mixture extracted with EtOAc and dried over MgSO4. Evaporation and crystallization from EtOAc/hexane gave an off-white solid (0.87 g, 56% yield); MS m/e 408 (M+H)+.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried over MgSO4
  3. customEvaporation and crystallization from EtOAc/hexane

Sources & evidence

ORD record
ord-80b229e035a54a33978f433cc08fb29a
Source dataset
uspto-grants-2006_12
Patent number
US07148247B2

Reaction notes

Loading…